Carbon Dioxide → HCID 86701981, compound

HRID 717962Notes

Reaction equation

HRID 717962 reaction equation
[C:1]([S@@:5](/[N:7]=[CH:8]/[C:9]1[S:13][C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:11][CH:10]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].C(=O)=O.[CH2:24]([Mg]Br)[CH:25]([CH3:27])[CH3:26]>ClCCl>[CH3:2][C:1]([CH3:4])([S@@:5]([NH:7][C@@H:8]([C:9]1[S:13][C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:11][CH:10]=1)[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:6])[CH3:3].[CH3:2][C:1]([CH3:4])([S@@:5]([NH:7][C@H:8]([C:9]1[S:13][C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:11][CH:10]=1)[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:6])[CH3:3]

Participants

6

Reactant 3

HCID 280Carbon Dioxide2×HCID 87383933HCID 87383933, compoundHCID 178418816HCID 178418816, compound

Product 2

HCID 86701981HCID 86701981, compoundHCID 86701982HCID 86701982, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S,E)-tert-Butyl 5-((tert-butylsulfinylimino)methyl)thiophene-2-carboxylate (1 g, 3.17 mmol) was dissolved in dichloromethane (15.85 ml) and chilled to −45° C. in an acetone bath to which dry ice had been added to achieve the desired temperature. Isobutylmagnesium bromide (2.0M in diethyl ether; 3.17 ml, 6.34 mmol) was added dropwise over ˜5 minutes. The mixture was stirred for 4 hours keeping the temperature between −40° C. and −50° C. by periodic addition of dry ice and then warmed to room temperature overnight. The mixture was quenched with saturated ammonium chloride (exothermic, bubbling) and extracted with dichloromethane (three times; considerable emulsion formed). The organic extracts were dried with sodium sulfate, filtered, concentrated and chromatographed to provide both tert-butyl 5-((R)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate and tert-butyl 5-((S)-1-((S)-1,1-dimethylethylsulfinamido)-3-methylbutyl)thiophene-2-carboxylate as separate compounds.

Workup

  1. additionhad been added
  2. customthe temperature between −40° C. and −50° C.
  3. customThe mixture was quenched with saturated ammonium chloride (exothermic, bubbling)
  4. extractionextracted with dichloromethane (three times; considerable emulsion formed)
  5. dry with materialThe organic extracts were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed

Sources & evidence

ORD record
ord-f577540272c746608036fb0d24f498fa
Source dataset
uspto-grants-2015_11
Patent number
US09193723B2

Reaction notes

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